EP1006146A1 - Compositions organopolysiloxanes réticulables en élastomères par élimination d'alcools - Google Patents

Compositions organopolysiloxanes réticulables en élastomères par élimination d'alcools Download PDF

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Publication number
EP1006146A1
EP1006146A1 EP99123224A EP99123224A EP1006146A1 EP 1006146 A1 EP1006146 A1 EP 1006146A1 EP 99123224 A EP99123224 A EP 99123224A EP 99123224 A EP99123224 A EP 99123224A EP 1006146 A1 EP1006146 A1 EP 1006146A1
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EP
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Prior art keywords
rtv
alkoxy
values
und
alkoxysilane
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EP99123224A
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German (de)
English (en)
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EP1006146B1 (fr
Inventor
Christian Dr. Finger
Norman Dorsch
Wolfgang Dr. Hechtl
Christian Baumgartner
Alfred Heinrich
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Wacker Chemie AG
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Wacker Chemie AG
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups

Definitions

  • the invention relates to low modulus vulcanizates RTV-1 alkoxy compositions, their preparation and use as Joint sealants for grouting natural stone.
  • organopolysiloxanes is intended in the context of the present Invention include dimeric, oligomeric and polymeric siloxanes.
  • Plasticizer-free RTV-1 materials have an unfavorable stress-strain behavior for use as permanently elastic joint sealing materials, since the stress values are too high, for example, when the strain is 100% ("module at 100% strain").
  • a high 100% modulus e.g. 0.6 N / mm 2
  • a high 100% modulus is synonymous with a strong increase in tension in the event of a joint expansion caused, for example, thermally, whereby the risk of adhesion failure, i.e. detachment of the elastic sealing material from the respective joint base, is also greatly increased.
  • a 100% modulus of 0.2-0.4 N / mm 2 should preferably be aimed for.
  • the stress expansion behavior of a silicone rubber vulcanizate is determined by the type and proportion of the filler and before all thanks to the number of networking nodes per unit volume certainly.
  • the module can be hydroxyl-terminated diorganopolysiloxane of RTV-1 systems.
  • the use if possible Long-chain polymers are limited by the fact that to achieve a soft pasty, stable consistency of the pastes containing filler the viscosity of the organopolysiloxane should not be too high, because then putty-stiff pastes result that are difficult to process.
  • the basic disadvantage of a plasticizer is that it is not connected to the vulcanizate network. He can therefore be characterized both by contact with a solvent be removed from the vulcanizate as well as from the Hike out vulcanizate on an adjacent surface and prove this. This process is particularly common when grouting of porous natural stone, such as marble, granite, alto quartzite strikingly clear because of a hydrophobization and darkening the joint edge zones takes place, which is of course undesirable. In principle, therefore, none should be used for natural stone grouting plasticized products are used.
  • the invention has for its object to be easy to process RTV-1 alkoxy compositions which are added to a plasticizer without the addition of plasticizers low module can be set easily to provide.
  • the process runs at high temperature even at room temperature Reaction rate selectively, so that shortly after Mixing components (A), (B1), (B2) and (C), for example after 10 minutes, the alkoxy terminated Organopolysiloxane, which is the product of the reaction of components (A) with (B1) and (B2) with elimination of Represents alkanol; if necessary after adding further Components can be used as RTV-1 alkoxy mass.
  • a Energy supply for example by heating the mixture, is not necessary. On a check that the implementation is complete can be dispensed with.
  • Another advantage of this method is that there are no side reactions and, for example, on linear HO-terminated organopolysiloxane (A) the formation of T and Q units were not observed.
  • the acidic phosphoric acid esters (C) have to be after the reaction not be deactivated immediately afterwards.
  • hydrocarbon radicals R are linear and cyclic saturated and unsaturated alkyl radicals such as the methyl radical, aryl radicals such as the phenyl radical, alkaryl radicals such as tolyl radicals and aralkyl radicals such as the benzyl radical.
  • Unsubstituted hydrocarbon radicals having 1 to 6 carbon atoms are preferred as the R radical, the methyl radical being particularly preferred.
  • the organopolysiloxanes (A) preferably have one Viscosity from 100 to 700,000 mPa.s, in particular from 20,000 to 350,000 mPa.s, each measured at 23 ° C.
  • Partial hydrolyzates of alkoxysilane (B1) are by hydrolysis and condensation of in particular 2 to 4 alkoxysilanes emerged. Partial hydrolyzates (B1) are for example Hexamethoxydisiloxane and hexaethoxydisiloxane.
  • the alkoxysilanes (B2) preferably have the general formula (IV) R 7 2 Si (OR 8 ) 2 on what R 7 and R 8 are monovalent C 1 -C 13 -hydrocarbon radicals which are optionally substituted by fluorine, chlorine, bromine, C 1 -C 4 -alkoxyalkyl or cyano groups.
  • R 5 and R 7 are each preferably unsubstituted C 1 -C 6 -hydrocarbon radicals, in particular methyl, ethyl and propyl radicals.
  • R 6 and R 8 are each preferably unsubstituted C 1 -C 6 -hydrocarbon radicals, in particular methyl, ethyl, vinyl and propyl radicals.
  • the acidic phosphoric acid esters (C) of the general formula (I) stabilize those terminated from the alkoxy groups Organopolysiloxane produced RTV-1 alkoxy masses in the Storage. In particular, the skin formation times of the RTV-1 alkoxy masses remain almost constantly stable and discoloration becomes prevented.
  • the acidic phosphoric acid esters (C) are based on 500 Parts by weight of the HO-terminated organopolysiloxanes (A) at 0.1 up to 50 parts by weight, especially 2 to 20 parts by weight added.
  • the addition of the alkoxysilanes (B1) and (B2) to the HO-terminated Organopolysiloxanes (A) are preferably carried out in one Excess in terms of stoichiometric ratios.
  • Around the reaction of the HO-terminated organopolysiloxanes (A) with Alkoxysilanes (B1) and (B2) run as completely as possible can preferably 10 to 60 parts by weight, in particular to 20 to 50 parts by weight of the alkoxysilanes (B1) and (B2) per 500 parts by weight of the HO-terminated organopolysiloxanes (A) be used.
  • alkoxysilanes (B1) and (B2) are in the with Organyloxy groups terminated organopolysiloxane and the RTV-1 alkoxy masses not a disadvantage and can therefore in Reaction product remain.
  • An excess of alkoxysilanes (B1) acts as a crosslinking component in the RTV-1 alkoxy compositions.
  • the reaction is preferably carried out at temperatures from +20 to + 50 ° C, especially at room temperature.
  • the response time depends on the alkoxysilanes used (B1) and (B2) 1 to 60 minutes.
  • the reaction speed in the implementation is aimed at one according to the reactivity of the alkoxysilanes used (B1) and (B2), on the other hand after the acidic phosphoric acid ester (C).
  • the particularly preferred implementation time is Room temperature 3-20 min, which is just for the production of RTV-1 masses in the one-pot process is of major advantage.
  • the RTV-1 alkoxy masses can contain further components known per se.
  • RTV-1 alkoxy compositions are bis (trialkoxysilyl) C 1 -C 12 alkanes in which the alkoxy radicals have the meanings of O R 6 , for example bis (triethoxysilyl) ethane.
  • condensation catalysts such as dimethylpolysiloxanes or phosphoric acid esters which are endblocked at room temperature by trimethylsiloxy groups, fungicides, resinous organopolysiloxanes, including such polysiloxanes, can be used in the preparation of the RTV-1 alkoxy compositions (CH 3 ) 3 SiO 1/2 and SiO 4/2 units, pure organic resins, such as homopolymers or copolymers of acrylonitrile, styrene, vinyl chloride or propylene, such purely organic resins, in particular copolymers of styrene and n -Butyl acrylate, in the presence of diorganopolysiloxane each having a Si-bonded hydroxyl group in the terminal units, may have been produced by polymerizing the monomers mentioned by means of free radicals, corrosion inhibitors, poly
  • Condensation catalysts are preferably used. It According to the invention, the RTV-1 alkoxy compositions can be any Condensation catalysts included, which have also been described below Exclusion of water storable, with access of water Room temperature produced to crosslink elastomeric masses have been available.
  • condensation catalysts examples include organic Connections of tin, zinc, zirconium, titanium and aluminum.
  • Butyl titanates and organic tin compounds such as di-n-butyltin diacetate, Di-n-butyltin dilaurate and Reaction products of at least two per molecule Oxygen bound to silicon, optionally by a Monovalent hydrocarbon radicals substituted by alkoxy groups as hydrolyzable groups containing silane or its Oligomer with diorganotin diacylate, being in these Reaction products through all valences of the tin atoms Oxygen atoms of the group ⁇ SiOSn ⁇ or by SnC-bound, monovalent organic residues are saturated.
  • the RTV-1 alkoxy compositions preferably contain fillers.
  • fillers are non-reinforcing fillers, i.e. fillers with a BET surface area of up to 50 m 2 / g, such as quartz, diatomaceous earth, calcium silicate, zirconium silicate, zeolites, metal oxide powders such as aluminum, titanium, iron or zinc oxides or the like Mixed oxides, barium sulfate, calcium carbonate, gypsum, silicon nitride, silicon carbide, boron nitride, glass and plastic powders, such as polyacrylonitrile powder; reinforcing fillers, ie fillers with a BET surface area of more than 50 m 2 / g, such as pyrogenically prepared silica, precipitated silica, carbon black, such as furnace black and acetylene black, and silicon-aluminum mixed oxides with a large BET surface area; fibrous fillers such as asbestos and plastic fibers.
  • the fillers mentioned can be hydrophobized, for example by treatment with organosilanes or siloxanes or with stearic acid or by etherification of Hydroxyl groups to alkoxy groups. It can be a kind of Filling material, it can also be a mixture of at least two Fillers are used.
  • the usual is sufficient for crosslinking the RTV-1 alkoxy masses Water content in the air.
  • the networking can, if desirable, even at higher or lower temperatures than Room temperature, e.g. at -5 ° to 10 ° C or at 30 ° to 50 ° C be performed.
  • the tension value at 100% elongation (100% modulus) is preferably according to DIN 18540 with the hardened RTV-1 alkoxy mass at most 0.45, in particular at most 4.
  • the RTV-1 alkoxy compositions according to the invention are therefore suitable excellent as sealing compounds for joints, including vertical joints, and the like Empty spaces e.g. 10 to 40 mm clear width, e.g. of Buildings, land, water and aircraft, or as Adhesives or putties, e.g. in window construction or at the manufacture of showcases, e.g. for production of Protective covers, or of rubber-elastic moldings as well for the insulation of electrical or electronic Devices.
  • Those according to the invention are particularly suitable RTV-1 alkoxy compounds as joint sealing compounds for grouting Natural stone.
  • 850 g of a dimethylpolysiloxane each of which has a hydroxyl group in the terminal units and a viscosity of 20,000 mPa.s at 23 ° C. with 12 g of a mixture of alkoxylated phosphoric acid esters of the formulas, are excluded from water (OH) 1 PO [(OCH 2 CH 2 ) 2-3 -O- (CH 2 ) 7-9 -CH 3 ] 2 and (OH) 2 PO [(OCH 2 CH 2 ) 2-3 -O- (CH 2 ) 7-9 -CH 3 ] 1 mixed.
  • the compound After homogenization in vacuo, the compound is in filled with moisture-proof containers.
  • the skin formation time of the mass during vulcanization has an initial value of 20 minutes; this value remains unchanged even after 28 d / 50 ° C.
  • the measurement of the module at 100% elongation of the mass according to the example in a bond prepared and cured according to point 3) gives a value of 0.50.
  • a joint between Altoquarzit panels produced according to point 4) shows no edge zone contamination after 6 weeks at 50 ° C.
  • 850 g of ⁇ , ⁇ -dihydroxypolydimethylsiloxane from Example 1 are mixed with 15 g of a mixture of alkoxylated phosphoric acid esters of the formulas (OH) 1 PO [(OCH 2 CH 2 ) 3-4 -O- (CH 2 ) 11-14 -CH 3 ] 2 and (OH) 2 PO [(OCH 2 CH 2 ) 3-4 -O- (CH 2 ) 11-14 -CH 3 ] 1 mixed.
  • the skin formation time of the mass during vulcanization has a starting value of 30 minutes; this value remains unchanged even after 28 d / 50 ° C.
  • the measurement of the module at 100% elongation of the mass in a bond prepared and cured according to point 3) gives a value of 0.35.
  • a joint between Altoquarzit panels produced according to point 4) shows no edge zone contamination after 6 weeks at 50 ° C.
  • the skin formation time of the mass during vulcanization has an initial value of 35 minutes; this value remains unchanged even after 28 d / 50 ° C.
  • the measurement of the module at 100% elongation of the mass in a bond prepared and hardened according to point 3) cannot be determined, since an elongation of 73% causes the mass to crack.
  • the modulus at 50% elongation is 0.56; the mass is extremely high modulus.
  • a joint between Altoquarzit panels produced according to point 4) shows no edge zone contamination after 6 weeks at 50 ° C.
  • Example 5 (Comparative Example Without Module-Lowering Additive with a lower crosslinker content and other compounding Order as example 4):
  • the skin formation time of the mass during vulcanization has an initial value of 20 minutes; this value remains unchanged even after 28 d / 50 ° C.
  • the measurement of the module at 100% elongation of the mass in a bond prepared and cured according to point 3) gives a value of 0.60.
  • a joint between Altoquarzit panels produced according to point 4) shows no edge zone contamination after 6 weeks at 50 ° C.
  • Example 6 comparative example with external plasticizer:
  • the skin formation time of the mass during vulcanization has an initial value of 20 minutes; this value remains unchanged even after 28 d / 50 ° C.
  • the measurement of the module at 100% elongation of the mass in a bond prepared and cured according to point 3) gives a value of 0.38.
  • a joint between Altoquarzit slabs produced according to point 4) shows severe edge zone contamination after 6 weeks at 50 ° C.
  • Example 7 comparative example with external plasticizer:
  • the skin formation time of the mass during vulcanization has an initial value of 20 minutes; this value remains unchanged even after 28 d / 50 ° C.
  • the measurement of the module at 100% elongation of the mass in a bond prepared and cured according to point 3) gives a value of 0.36.
  • a joint between Altoquarzit slabs produced according to point 4) shows a very strong edge zone contamination after 6 weeks at 50 ° C, which is more pronounced than in Example 6.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
EP99123224A 1998-12-02 1999-11-25 Compositions organopolysiloxanes réticulables en élastomères par élimination d'alcools Expired - Lifetime EP1006146B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19855619A DE19855619A1 (de) 1998-12-02 1998-12-02 Unter Abspaltung von Alkoholen zu Elastomeren vernetzbare Organopolysiloxanmassen
DE19855619 1998-12-02

Publications (2)

Publication Number Publication Date
EP1006146A1 true EP1006146A1 (fr) 2000-06-07
EP1006146B1 EP1006146B1 (fr) 2002-02-13

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EP99123224A Expired - Lifetime EP1006146B1 (fr) 1998-12-02 1999-11-25 Compositions organopolysiloxanes réticulables en élastomères par élimination d'alcools

Country Status (8)

Country Link
US (1) US6254811B1 (fr)
EP (1) EP1006146B1 (fr)
JP (1) JP3419718B2 (fr)
KR (1) KR100359705B1 (fr)
CN (1) CN1125139C (fr)
AT (1) ATE213261T1 (fr)
DE (2) DE19855619A1 (fr)
ES (1) ES2172282T3 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7094858B2 (en) 2003-04-29 2006-08-22 Wacker-Chemie Gmbh Process for the preparation of crosslinkable materials based on organosilicon compounds
US7795367B2 (en) 2004-04-27 2010-09-14 Wacker Chemie Ag Method for producing siloxane copolymers
WO2012134788A1 (fr) * 2011-03-31 2012-10-04 Dow Corning Corporation Compositions contenant des catalyseurs phosphates et procédés pour la préparation et l'utilisation des compositions
EP2557107A1 (fr) * 2011-08-12 2013-02-13 Evonik Goldschmidt GmbH Procédé de fabrication de polysiloxanes dotés de groupes contenant de l'azote
DE102014222826A1 (de) 2014-11-07 2016-05-12 Wacker Chemie Ag Vernetzbare Organopolysiloxanzusammensetzungen

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US6803409B2 (en) * 2002-05-29 2004-10-12 John Robert Keryk Organopolysiloxane copolymer and method of preparing
DE10259613A1 (de) 2002-12-19 2004-07-08 Wacker-Chemie Gmbh Organopolysiloxanzusammensetzungen und deren Einsatz in bei Raumtemperatur vernetzbaren niedermoduligen Massen
JP3897769B2 (ja) * 2003-04-24 2007-03-28 花王株式会社 へそ凹部清浄剤
DE102004014216A1 (de) * 2004-03-23 2005-10-13 Wacker-Chemie Gmbh Vernetzbare Massen auf der Basis von Organosiliciumverbindungen
KR20090094377A (ko) * 2006-12-19 2009-09-04 바스프 코팅스 악티엔게젤샤프트 높은 내스크래치성 및 풍화 안정성을 갖는 코팅제
DE102009028142A1 (de) * 2009-07-31 2011-02-03 Wacker Chemie Ag Bei Raumtemperatur durch Kondensation vernetzende Siliconmassen
WO2011133408A2 (fr) * 2010-04-23 2011-10-27 Henkel Corporation Copolymère de silicone et d'acrylique
US20140024774A1 (en) * 2011-03-31 2014-01-23 Simon Cook Condensation reaction curable silicone organic block copolymer composition containing a phosphonate catalyst and methods for the preparation and use of the composition
WO2012134784A1 (fr) * 2011-03-31 2012-10-04 Dow Corning Corporation Compositions contenant des catalyseurs phosphonates et procédés pour la préparation et l'utilisation des compositions
US8481655B2 (en) 2011-07-27 2013-07-09 Wacker Chemical Corporation Copper complexes of amino-functional organosilicon compounds and their use
CN102898883B (zh) * 2011-07-29 2016-08-24 道康宁(中国)投资有限公司 涂料组合物、使用其涂覆材料表面的方法、以及具有其的表面处理的材料
CN105392831A (zh) * 2013-07-02 2016-03-09 莫门蒂夫性能材料股份有限公司 可湿固化组合物
CN103467745B (zh) * 2013-09-03 2015-08-05 成都硅宝科技股份有限公司 末端烷氧基聚硅氧烷的制备方法
US9284413B2 (en) * 2013-11-15 2016-03-15 Wacker Chemical Corporation Process to produce stable alkoxy terminated aminofunctional silicone fluids
US20160185911A1 (en) * 2014-12-24 2016-06-30 Industrial Technology Research Institute Polysiloxane and hybrid material and method for manufacturing the same

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WO1996027636A1 (fr) * 1995-03-03 1996-09-12 Bayer Aktiengesellschaft Masses de polysiloxane reticulees par condensation, leur procede de preparation et charges a surface modifiee

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US4755578A (en) * 1982-12-13 1988-07-05 General Electric Company Alkoxy-functional one-component RTV silicone rubber compositions
EP0608888A1 (fr) * 1993-01-28 1994-08-03 Wacker-Chemie GmbH Compositions d'organopolysiloxanes réticulables en élastomères
WO1996027636A1 (fr) * 1995-03-03 1996-09-12 Bayer Aktiengesellschaft Masses de polysiloxane reticulees par condensation, leur procede de preparation et charges a surface modifiee

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7094858B2 (en) 2003-04-29 2006-08-22 Wacker-Chemie Gmbh Process for the preparation of crosslinkable materials based on organosilicon compounds
US7795367B2 (en) 2004-04-27 2010-09-14 Wacker Chemie Ag Method for producing siloxane copolymers
WO2012134788A1 (fr) * 2011-03-31 2012-10-04 Dow Corning Corporation Compositions contenant des catalyseurs phosphates et procédés pour la préparation et l'utilisation des compositions
EP2557107A1 (fr) * 2011-08-12 2013-02-13 Evonik Goldschmidt GmbH Procédé de fabrication de polysiloxanes dotés de groupes contenant de l'azote
US8796198B2 (en) 2011-08-12 2014-08-05 Evonik Degussa Gmbh Process for producing polysiloxanes with nitrogen-containing groups
DE102014222826A1 (de) 2014-11-07 2016-05-12 Wacker Chemie Ag Vernetzbare Organopolysiloxanzusammensetzungen
US10316149B2 (en) 2014-11-07 2019-06-11 Wacker Chemie Ag Crosslinkable organopolysiloxane compositions

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JP2000169587A (ja) 2000-06-20
DE19855619A1 (de) 2000-06-08
DE59900857D1 (de) 2002-03-21
KR20000047761A (ko) 2000-07-25
JP3419718B2 (ja) 2003-06-23
ES2172282T3 (es) 2002-09-16
CN1125139C (zh) 2003-10-22
KR100359705B1 (ko) 2002-11-08
US6254811B1 (en) 2001-07-03
ATE213261T1 (de) 2002-02-15
EP1006146B1 (fr) 2002-02-13
CN1255514A (zh) 2000-06-07

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